Syncing Apple's iPhone calendar to Apple's iCal (internet calendar program) works as advertised.
However, attempting to sync with Google's calendar, and outlook 2007 proved inconsistent at best.
I had been using iCal without issue, but have been asked on several occasions for help with Gmail / outlook.
After a couple days of troubleshooting, I found the easiest answer was to be centered on Google's calendar, with everything else syncing with the gmail (Google eMail) account / password.
[Gmail is a free email / calendar service and provides over 7GB of storage.]
Google Calendar Sync is a freeware windows program (background process) which will sync Google's calendar to microsoft outlook at a specified interval. (outlook for Mac hasn't been released yet.)
Setting up Google calendar (and syncing to iCal):
1) Export your iCal calendar.
(Run iCal, click 'View' click 'Show Calendar List' if it isn't already, then click to highlight your calendar on the left margin, click 'File', select 'Export...', and note where the file is saved.)
Note: You can combine multiple calendars by exporting them individually, and then importing them after selecting your primary calendar you want from the left iCal margin.
2) Login to Gmail, click Calendar. (upper-left corner of the webpage)
Go through the two second setup for the calendar if you haven't created one.
3) Click 'Settings' under 'My Calendars' in the left margin, and click 'Choose File' from the resulting dialog box.
4) Choose your previously exported iCal calendar from its download location. (Step 1)
Your calendar is now on Google.
5) Once the chosen calendar is imported, run iCal, click 'Preferences' and select 'Accounts'; in the resulting dialog box, click the little plus sign to add your Gmail address and password.
Your calendar is now syncing to iCal.
6) Once the calendar appears (under your email address in iCal's left margin), you can compare it to your original by checking the boxes next to each account in the left margin.
Note: You can delete the original you had exported earlier, as the new Gmail one is a duplicate (master), otherwise, leave it unchecked to avoid seeing the duplicate entries.
Syncing Google calendar to Apple's iPhone:
Click 'Settings'
select 'Mail, Contacts, Calendars'.
Add your Gmail account if you haven't already.
Select the Gmail account, click the 'Calendars' switch to 'On'
Note: Google offers "push" for calendars, selecting 'Push' from the 'Fetch New Data' option (under the Accounts listing for the 'Mail, Contacts, Calendars' setting), will provide faster syncing, at the cost of slight battery expense.
Your calendar entries will appear on your iPhone, iCal, Google calendar, and outlook after the specified allotted time set to sync by the individual programs.
...what a mess, time for a drink.
